Sodium hydride → HCID 21498783, compound

HRID 1729987Notes

Reaction equation

HRID 1729987 reaction equation
[H-].[Na+].[C:3]([N:11]1[CH2:20][C:19]2[C:18](=[O:21])[NH:17][C:16]3[CH:22]=[C:23]([O:28][CH3:29])[C:24]([O:26][CH3:27])=[CH:25][C:15]=3[C:14]=2[CH2:13][CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.Cl[CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>CS(C)=O.O>[C:3]([N:11]1[CH2:20][C:19]2[C:18](=[O:21])[N:17]([CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[C:16]3[CH:22]=[C:23]([O:28][CH3:29])[C:24]([O:26][CH3:27])=[CH:25][C:15]=3[C:14]=2[CH2:13][CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 21793849HCID 21793849, compound

Product 1

HCID 21498783HCID 21498783, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A suspension of 0.066 m NaH in 75 cc dimethylsulfoxide was cooled in a cold water bath and treated portionwise with 10 g (0.028 m) of 3-benzoyl-1,2,3,4-tetrahydro-8,9-dimethoxy-benzo[c][2,7]naphthyridin-5(6H)-one in 10 min. After stirring for 5 min the reaction was treated with 5.5 g (0.03 m) of N-(2-chloroethyl)piperidine hydrochloride in 2 min. After stirring an additional 2 hr the reaction was diluted with water to 800 ml to give 11.5 g of crude solid product, used as is for hydrolysis.

Workup

  1. temperaturewas cooled in a cold water bath
  2. stirringAfter stirring an additional 2 hr the reaction

Sources & evidence

ORD record
ord-d6b7246eb86c4aa8b1994b8247221dc7
Source dataset
uspto-grants-1976_11
Patent number
US03991064

Reaction notes

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